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Her foray in to the world of Sugar Daddies was short lived, to say the least. Except she still really needed to make some extra cash. She had unintentionally landed two side gigs on top of her regular 9-5 office job. She nannied for a family from her previous employment at a daycare centre in town, and she had also inadvertently started an under the table pet sitting business. She was making decent enough money, but still, her two side jobs didn’t come anywhere near close enough to supplementing the extra money she needed to get herself on her feet.

Speaking of feet… Throughout the entirety of her time on dating apps, she’d come in contact with a wide variety of odd characters (see any random Chapter for proof). One of the biggest subsets of these dating app guys, were the foot fetishists.

She had the same photos of herself on all the apps, only one in which you could see her feet. Needless to say, that one photo got a lot of action. She had always tried to stay open minded when it came to people’s kinks. Surely she liked things in the bedroom that would make her blush if she were to be outed or mocked for it. However, she had become skeptical of the foot fetish guys. Specifically because of her interactions with Chad the Douchebag (see Chapters 41 through 43).

Fortunately, not all shoes fit the same foot [fetishist]. Some of the guys that commented on her feet were definitely weird and would say gross things like wanting to put her whole foot in their mouth or something, others were fine and polite and just told her she had cute feet.

It was late summer when she happened to have gotten like 3 or 4 messages about her feet in one week. A record, surely. Finally, she decided to accept one guy’s chat invites and began to ask him about it.

This particular guy had followed her on Instagram, and he started their conversation with a general “Hey, how’s it going?” Within moments of her replying, however, he immediately brought up that he liked her feet. After a bit of back and forth, she just flat out asked him, “What’s so great about feet?”

A few moments later, she received a fairly articulate explanation of what made feet so special to him. He said, “I like the fact that it shows me the woman takes care of herself and her body, from head to toe. That, to me, is a big turn on. I also like the different things you can do in the bedroom, Kinkier sex, ect…”

He asked what he meant by different things in the bedroom. Because to her, getting fucked with a foot was not a good time. He replied, “I incorporate foot play in a sensual manner that always seems to work for me. I would gladly give you a foot massage…”

That was enough for her. She had gotten a pretty reasonable explanation out of him. It made sense to her that he could see feet as a form of good health. When she had been nearly 70lbs heavier, back when she was with her ex, her feet were comparable to the Sahara, just unbelievably dry. Her heels basically had mouths, they were so deeply cracked. Once she started taking care of herself, her feet healed themselves. And clearly they were lookin’ good, considering all the attention they had been getting.

As she chatted with this particular foot admirer, a light bulb went on in her head. Being a Sugar Baby might not have been in the cards for her, but was the Universe presenting her with yet another financial opportunity? If her feet were as cute as these guys made them out to be, surely she would be missing a great opportunity to make some extra cash by not selling foot pics.

Her insightful new pal just so happened to be in the foot pic business, or so he claimed. He offered to help her out by giving her tips and tidbits of how to take good foot pictures, and where to sell them. “You only want free feet pics,” she said when he offered to help her. “Hey, a little bit for you, a little bit for me.. It’s a win/win” he replied. She agreed to let him know when she was ready to get the ball rolling on selling some photos. But first, she needed a pedicure!

Her friend was getting married in two weeks, so she decided to wait until she got her glam done for the event, and would take pictures then. The time finally came, and she chose a deep purple for her toes. As the aesthetician finished her last toe, she inspected them and realized she absolutely hated the colour. It was more brown than purple and she knew it was not a colour worthy of being photographed and sold.

Her aesthetician sensed her unhappiness and was actually insanely generous in offering to redo them. It would just cut in to her manicure time and she wouldn’t get the whole relaxation part. So kind! She grabbed a deep grey/blue colour, very appropriate for the season, she thought. The woman finished and she was satisfied, though still didn’t love it and wished she had just gone with a crowd pleasing pink, or something more likely to get interest. These dark fall colours didn’t seem to hit.

She went home and, fortunately, her parents were out. The perfect time to take foot pics without having to sneak around. She thought of where might be a good setting, and settled on the backyard, in the grass. That seemed whimsical or like.. natural? Whatever, that’s where she went. Believe it or not, it was harder than she had thought it would be to take a good foot pic. She could never seem to get the right angle, she would sometimes get her butt in the background and it was not a flattering view. She took as many as she could before she got too frustrated and wanted to throw her phone. She decided to take a break and would try again another day.

That next week flew by and then all of a sudden, it was her friend’s wedding day. Feet pics were not a priority that week. The wedding was such a gorgeous event. The atmosphere was magical, the ceremony was moving and didn’t run long, the food was delicious and the dancing was a party and a half. She was the only single gal among her friends, per yooj. But one of her friends had recently had a baby, and left the wedding early. It was her friend’s suggestion that her husband stay and celebrate the happy couple, so he ended up being her +1. And what a great +1 he was! She had a great time with him, and all their friends.

The night was winding down and she was feeling pretty friendly after all the wine. She had a good buzz going but still had her wits about her. She was genuinely just happy and enjoying the night. The wedding was held at a beautiful restaurant downtown, right on the water. She walked outside on the deck to get some fresh air and enjoy the view, when she ran in to one of the bridesmaids, Kaitlin, who was talking to a cute guy she didn’t recognize. Kaitlin greeted her and introduced them, “Hey! This is my brother, Jordon. I don’t think you’ve met yet.”

They shook hands and she introduced herself. Jordon was really close with his sister, Kaitlin, and as such had gotten to know her friend, the bride, very well. She had heard a little bit about Jordon before that night. She knew that he had been recently divorced, and was somewhat newly single, too. Her friend had never introduced them for fear of them potentially hooking up and then causing drama in her friend group, but her friend also knew that she and Jordon both had some things to work out from past relationships before either of them would be in a place to enter any kind of new relationship. She didn’t begrudge her friend for keeping them apart, and she truly preferred this way of meeting him.

As they talked, all of a sudden they realized that Kaitlin had disappeared and neither of them had really noticed her go. They clearly had a lot in common in regard to their relationship status, and they were both enjoying the single life after both having been through the shit with their exes.

She and Jordon had been chatting directly in the middle of the deck, and when she realized they might be there for a while, she decided she wanted something to lean on and suggested they move to the railing. As they changed locations, she looked up at him and he just kissed her.

It was so unexpected but so welcome. And holy fuck, he was a great fucking kisser. They made out for what felt like an eternity and a split second all in one, when all of a sudden they heard, “Jordon! Dad’s here to pick you up!” They both burst out laughing. What a mood killer. But wow. What a whirlwind.

This meet cute was not at all how she saw her night ending, and all of a sudden she was filled with eager excitement and butterflies. They followed each other on Instagram, and they shared one last passionate kiss before he ran away like Cinderella at midnight.

She hurried back inside to the bathroom to regroup. What the hell just happened! Was she in a romantic comedy? Meeting guys organically in real life just doesn’t happen.. does it?

Continue to Chapter Seventy Three

Her evening with Jon, for the most part, was a good time. Except she was getting really tired of dating or hooking up with younger guys. She enjoyed how desired she felt when she was with them, but the novelty was wearing off. She wanted an older guy, or at least someone her own age. Someone who was in a similar place in their life as she was, with whom she could possibly start a real relationship.

Well, those guys didn’t seem to exist. Anyone she did match with who was her age or older were either married and ENM, or divorced and bitter, and only looking for fun. Behaving in ways that helped her understand why they were divorced. At the same time, her other woes in life were creeping in, as well. Specifically, her financial struggles.

She had never been very good with money. However, since moving home, she had been able to pay off her student loan, as well as finance a car. Her big issue now had been the credit card debt she shared with her ex. Over the seven years they were together, she let him accumulate so much debt in her name, that she was still drowning in bills almost three after leaving him. She was diligent at making her payments, but the interest on both cards were just killing her and she had made very little headway in chipping away at the principle.

Finally, after several years of being back home, she was able to secure a consolidation loan to pay off the thousands of dollars she owed on her cards. Her new payments for her loan were much less than she had been paying, and the interest was much more reasonable. She was so relieved to finally be on track at getting her debt down. Even still, inflation and cost of living had increased astronomically, and she still struggled on the daily to even just get herself to work with gas prices being so high, just as one example.

One day, as she scrolled through Instagram on her lunch hour, an Influencer she followed was promoting her latest podcast, an episode entitled, “Sugar Baby Confessionals” … or something to that effect. The money struggle is REAL, and the idea of funny stories about young, smart, empowered women dating older men to better themselves financially actually really intrigued her.

She downloaded the podcast and gave it a listen. During one of the confessions, one of the women mentioned the website on which she had met her Sugar Daddy. Overwhelming curiosity compelled her to go check it out, but she couldn’t look through the selection of rich old men without creating a profile.

She never thought she would ever consider it – having a Sugar Daddy? Being a Sugar Baby? That was for dirty old men and gold diggers. Except here she was, mid-30’s, living with her parents going on 3 years, financial independence continuously feeling out of reach. She felt desperate. Was this a sign from the Universe that she was meant to pimp herself out to dig herself out of her financial hole?

Probably not. But like.. maybe?

She caved and decided to make a profile. She added the six required photos, having cut off her head in all of them to protect her anonymity. It also allowed a private album to add full face pics in case you connected with someone and wanted to share your identity. The only way to see that album is to request access, and wait for the other person to approve or deny.

She filled out the bio as vaguely as possible, and began to navigate the website. Within a few minutes, her photo requests had filled up and she had at least a dozen messages. Some of the men had blurred photos, some not. Some were as old as late 70’s, others as young as mid-30’s. Some were actually decent looking, most were old and creepy.

She scanned through the messages and found a somewhat decent looking guy. Late 40’s, only slightly balding. Heavier, short, but very rich. His message was friendly and he seemed sweet. What harm could it do to reply?

They started chatting and he immediately showered her with compliments. He asked her what she was looking for, to which she replied, “I have no idea. First timer. Just seeing what this is all about…” So he shared his story, instead.

He explained that he had been a Sugar Daddy for 11 years, and that he’s married but his wife was asexual due to a disability. He was looking to connect with someone to meet for intimate dates once or twice a month, and to reward with gifts or “donations”, as he called it, towards whatever she was struggling with financially. In her case, that would be donations to her Pay-Off-Her-Loan or Buy-a-House funds. He also bragged about his oral skills, and mentioned that he has “an extremely huge dick” – direct quote.

Well, now then. Doesn’t that just sound like the perfect scenario for someone looking for that kind of arrangement? She was intrigued. How bad could it be? Pretend to be into this not-great-looking rich guy, get off a bunch of times, and leave with $X to put towards her finances. Maybe she could be down for that?

After an entire day of chatting on the website, he asked if she would mind switching to Snapchat so they could converse more easily. She was hesitant, but agreed. Once they had added each other, he immediately asked for nudes. She declined, and asked for some better face pics before she agreed to send him anything.

He sent her two more pics. Both typical, older guy selfies. Like what your weird uncle might put as a Facebook profile pic. Still decent looking. Now that she had a more concrete idea of who she was talking to, she agreed to send him another pic. Not nude, she was wearing a bikini top and shorts, and he fell even harder for her. Furiously typing out compliment after compliment. Damn. She could get used to this!

He then asked her, “So are you sure you don’t think I’m like, gross?” She paused and really contemplated as to how to reply. She knew she had to be honest, and she was aware that some guys like this often get off to being put down. Not that that’s what she wanted to do, but her honest opinion was not necessarily complimentary.

She told him that no, he wasn’t her regular type, but that he seemed nice and she had been enjoying their conversation. She also reminded him that she was new to this and asked that he be patient as she got herself accustomed to the idea of this type of arrangement.

He replied saying, “I’m no one’s type. I’ve never had sex without paying for it…” She knew she was about to get sucked in to a pity party, but she still took the bait and said, “Well how can that be true? You’re married, aren’t you? Your wife has to have seen something good in you to marry you?” To which he replied, “She’s from another country, it was a a long distance, online arrangement. She’s also blind. The only woman who was ever willing to give me a chance can’t see how ugly I am. And even she doesn’t want to fuck me…”

She’s also what!? Blind!!?? How do you respond to that!?

It was both hilarious and kind of heart breaking at the same time. She took her time to formulate a non-offensive reply, and decided to go with, “Well, I’m really sorry to hear that. Sounds like you’ve had a rough go…”

He took a littler longer to reply than he had been, but then said, “okay take care”. She was confused. How could he go from one moment saying he wanted to spoil her and do all these sexual things to her, to then just blowing her off. At the same time, no way was she about to beg some sad, lonely, old guy to continue chatting with her. So she replied, “Oh… ok? take care.”

He replied quickly saying, “Well you said I’m not your type…” She was somewhat taken aback because she figured he would have expected an answer like that. She also felt that her reply had been fairly kind, and she was trying hard not to be hurtful. She took a moment to organize her thoughts, then replied:

“You asked me a question, and I gave you an honest answer. I told you that no, I don’t typically go for guys like you, but I also said that you seemed nice and I was enjoying the conversation. We met on a Sugar Daddy website. We’ve chatted for several hours now. Whatever arrangement that we might have come to would have been an understood exchange of financial assistance for physical intimacy, regardless of whether or not you’re my type. But you’ve ruined it now. I’m not here to play therapist, but I wish you all the best.”

As soon as she hit send, she decided that that was enough of a glimpse in to the Sugar Daddy world for her. Plus, she knew deep inside that she wouldn’t have been able to have sex with someone under those circumstances, even if she was getting paid well for it. Not only that, she didn’t have the time or the mental bandwidth to be someone’s emotional support lay.

She blocked and deleted him from Snapchat, and then deleted her profile on the website. So much for that financial boost. Not to worry, though. The Universe had another trick up it’s sleeve…

Continue to Chapter Seventy Two

Now that she and Jon had reconnected, they barely stopped chatting throughout the next two weeks. Just sexting and dirty talk morning, noon and night. It was exhausting but also fun and exhilarating. For a somewhat inexperienced 26 year old, he could definitely write a sexy message. He knew what she liked in the bedroom, and he had a knack for articulating that through text.

He would text her during her work day and tell her to go take a dirty pic for him in the bathroom, for example. When she would refuse, he would become more dominant, using all the right words to make her “obey”. Was she stripping naked in her work bathroom? Absolutely not. But a sexy mirror selfie here or there never hurt anyone.

By the time they were finally able to pick a date that worked for both of them, the sexual intensity of their conversations had increased so much that she was a little bit nervous about meeting up with him. Nervous and excited.

At the same time, though, she had already hooked up with him twice before, neither encounter having left her blown away. Why go back, you ask? Well first of all, no one else was banging down her door asking her out again. Jon paid attention to her, made her feel sexy. He had also been boasting about how good it was going to be when they finally did meet up again, telling her of all the things he wanted to do to her. He even said he had a sexy surprise waiting for her. She was horny with anticipation.

Finally, the day arrived. She drove over to his place just before dusk, and he met her outside, as per yooj. Turns out he didn’t have the house to himself like he had said he would, so he took her on a stroll around a nearby park to smoke a joint and to catch up face to face, without the shield of a cell phone screen to buffer any awkward moments.

He started talking and the first thing she thought was , “Holy fuck his voice is so deep!” she truly did not remember him having such a manly voice. It was a welcome juxtaposition to the tall, scrawny looking man-child she was staring at. She had remembered he was a bit skinny, but forgot that he was actually like, shoulder-blades-poking-out skinny. She wasn’t body shaming him or anything, it just made him look so young! (Which he was…)

They sat on a bench at the park by his house, smoked his joint and chatted about current events. He was bringing up anything and everything that had been going on around the world lately. She remembered that that was something she liked about him. Even though he was young, he knew a lot about a lot, and was an excellent conversationalist. Skinniness be damned. This guy was smart, had a sexy voice, big strong hands, and knew how to turn her on. She was now stoned, and even more excited to get this party started.

They made their way back to his house, and he ushered her quickly through the side door and downstairs, as not to run in to his mom. They went in to his room and he closed the door behind them. He offered her some wine but she asked for water instead. She was already pretty stoned and didn’t want to get too fucked up, especially since she’d have to drive home in the somewhat near future. He ran upstairs to grab the drinks, and she could hear him dismissing his mom who was very likely grilling him on who this random girl was that he had brought home.

He returned a few minutes later with their drinks, and began to throw together a quick playlist. By playlist, it was literally just a queue of all Kanye songs. Not a fibre in her being wanted to listen to anything Kanye, but she wasn’t there for the music. She figured that was just to drown them out so his parents wouldn’t hear them upstairs. Except he didn’t get things going after having made the playlist. He grabbed his beer, sat down on the couch next to her, and began shootin’ the shit again. Um, hellooo? Where’s all the sexiness? Where’s the surprise? Was he just all talk, no action?

After a few minutes of him basically talking to himself about Putin, or whatever other current event he had trailed off on, he must have noticed that she was getting a bit bored because suddenly his beer was down and his hands were all over her.

They were sitting side by side, so he had sort of turned her over and brought her left leg up and over on to him. They made out intensely has he struggled to get his hands down her pants. Stupid high waisted leggings! After several minutes of sloppy foreplay, she suggested they move it to the bed.

“Lay down” he ordered her. Oooh, yes sir! she thought to herself. Finally!

He told her not to move as he rummaged through a bag on the floor by his bed. He then whipped out a collar and some rope. Her eyes lit up. Maybe he wasn’t all talk, after all?

As he started to put the collar on her, she realized that this was not a heavy duty sex collar. It was a fucking cat collar he had gotten from the dollar store! Not exactly what she had had in mind, but it would have to do. After several minutes of him struggling to fasten the buckle, (because it was a tiny little pin thing, meant for a CAT not a HUMAN WOMAN!), he then moved on to the rope.

She really enjoyed having her hands bound and restrained (especially after her sexy encounter with Kyle several months prior), but this wasn’t it. Jon hadn’t brought out any fancy rope specifically made for sex. Instead, he whipped out some neon yellow shit rope he bought at Home Depot. Not only was it coarse against her skin, it was fucking long! It took him forever to wrap around her hands and tie them tight enough that she couldn’t move her wrists apart. He also didn’t have anything to tie her to, so her wrists were restrained, but her arms were loose. Not what she had hoped for, but again, it would have to do.

Once she was sufficiently “subbed”, for lack of a better term, Jon was ready to start playing. He grabbed the leash that was attached to the collar, and pulled her up towards him for a kiss. The leash immediately broke. Shocker. She fell back on the bed and burst out laughing, and then so did he. This hook up was turning out to be as messy as the others, and she wasn’t even drunk this time.

Jon gave up on the leash and collar, and got himself back in the game. In a deep, sexy voice, he ordered her to turn over. She did as she was told. Now she was bent over the bed, laying on her stomach, holding herself up by her elbows, her wrists still tied.

He started playing with her ass which like, some might find sexy, but she certainly did not. Anything to do with ass play was just not her vibe. But she was really trying to stay in it. She wanted to play the “submissive” partner, while he “dominated” her. The reason for the quotes is because, she definitely did not feel submissive, nor did she feel like she was being dominated.

She was actually a little bored. She let him do his thing – kissing her, trying to pleasure her from behind… all the while she was twiddling her thumbs on her propped up elbows. While she was less than enthused, he apparently found it mind blowing.

All of a sudden, out of nowhere, she heard those unmistakable noises of a guy getting off, and then BAM! She felt a warm, liquid sensation all over her ass and back. She jerked her head around and saw Jon hunched over her, catching his breath.

It took everything in her power not to a) burst out laughing, but also b) get super fucking pissed! All those sexy conversations, all his big talk about blowing her mind, etc… All of that just for him to bust a nut after a whopping like, 7 minutes? So lame!

It turns out, in an ill advised attempt to make this encounter more thrilling, Jon had abstained from self pleasure for the previous four days before their hook up. The guy hadn’t jerked off in FOUR DAYS! No fucking wonder he finished early!

She had never been one to be able to hide her true feelings, so he could definitely tell she was disappointed. He hurried to grab something to clean her up – the shirt he had been wearing seemed like a fine choice. He wiped her up and as she attempted to stand, thinking it was over, he pushed her back down and in his deepest, sexiest voice, ordered her to turn over on her back.

Now things were sure to heat up, right?… Right??

With his right hand, he started pleasuring her just the way she liked it. With his left, he started to explore the rest of her body, focusing primarily on just one of her breasts. It got to the point where it felt like he was trying to fucking milk her, so she said in her sexiest whisper, “choke me”. His eyes lit up and he immediately grabbed her throat.

What would normally intensify her feelings of pleasure, this time just tickled her and made her want to burst out laughing. You know when someone tells you to rub your belly with one hand and tap your head with the other? It’s a real mind fuck, right? Well that seemed to be what was happening for Jon.

While his right hand rubbed her lady bits vigorously, his left hand started doing the same thing to her throat. Picture a puppeteer opening and closing his hand to make the puppet talk. That’s what he was doing to her throat while he “choked” her. Not sexy.

HOWEVER, something finally clicked between them and her sensations started to build, and Build, and BUILD! All of a sudden, there was an explosive sensation and she was feeling pleasure she hadn’t felt in a really long time. She looked up at Jon, and a smile spread across his face like a kid at Christmas. His eyes just lit up with the pride he felt in making her explode like that. They were both relieved that this encounter didn’t end with only one of them having a good time.

He collapsed beside her, still smiling from ear to ear, and she just lay their catching her breath. “You’re welcome” he said cockily. She gave him an exasperated eye roll. As pleasurable as that was, she knew she could have gotten herself there in less time, and with less mess.

She excused herself to the bathroom and got herself fixed up, then got dressed. Though she felt good now, she was ready to leave. However, she had told her parents she was going out with a friend, and at this point she had been gone only an hour and a half.

Jon was in no hurry to send her packing, so now that they had gotten the sexual tension out of the way, they were free to hang out and enjoy each other’s company. Meaning he picked up right where he had left off, rambling on about current events again, while she just sat there, counting down the minutes. His conversation skills had dwindled throughout the evening, and what she found intriguing before, just annoyed her now.

An hour or so later, they both agreed that it was time for her to go. He walked her out to her car and kissed her goodnight. Sometimes Jon could be so smooth. Other times, he seemed like an inexperienced goof ball. Overall, she felt like this was a decent enough little tryst. But man oh man, did she long for the touch of an older, experienced guy for whom she wouldn’t have to spell things out… And who could keep his composure for longer than 7 minutes.

Continue to Chapter Seventy One

She had taken the Friday off after her girl’s night because she knew she would probably be feeling rough. And now, especially after meeting up with Jason, she couldn’t have been more relieved to not have to work.

She had received that message from Jason pretty much first thing in the morning, so it had kind of started her day off on the wrong foot. She had made an appointment at the bank for that afternoon, so instead of dwelling on his abrupt end to their situation-ship, she decided to just relax and enjoy her morning off.

As she finished her breakfast and got comfortable on the couch to watch some daytime trash TV, she saw her phone light up. It was a message from Youssef. She honestly had never expected to hear from him again, figuring he would have been too embarrassed after their late night conversation. But here he was, texting her on a Friday morning, asking what she’s up to.

At first she was thrown aback because it was a work day. Why would he be messaging her now? Normally she would have been working and she felt like a Friday morning was a stupid time to message someone for a booty call. Except, she wasn’t working. And apparently neither was he.

She replied that she had taken the day off, but that she had an appointment later that afternoon. He had also taken the day off, and was basically begging her to come over. She thought about it, and even though his anxiety attack had really put her off, her disappointing encounter with Jason had also left her unsatisfied (even if she did finish). She agreed to come by Youssef’s place, and would go to her appointment afterwards.

She was still moving a bit slow from all the drinking the night before, but she made her way in to the shower and got herself ready, and was at Youssef’s within the hour. She walked in to find him watching porn on his big screen in the living room. In any other scenario, she would have been right out the door again. But that’s literally what she was there for, so she moved past it. She did make him mute it at least, though.

They got right down to business. He was insatiable. He couldn’t get enough of her. As he kissed her deeply and passionately, she immediately noticed his jaw popping. It was then that she realized – this guy was (or had been) high on blow.

“What time did you go to bed last night?” she asked. He gave her a guilty look and replied, “I haven’t yet…” No wonder he was so fucking horny. She decided to also move past that. She would have hated to have wasted a trip downtown in her hungover state, but was still kind of turned off. Making out with a guy who tastes like aspirin while his jaw pops every few seconds was really not her idea of a good time.

Aside from that annoyance, she quickly remembered what she did like about Youssef… he had great hands. He explored her body just the way she liked it, and once his hands reached down her pants, she was over it and ready to go. They played with each other non stop for over an hour. Again though, no sex. For someone who was so afraid of getting women pregnant, but who was constantly horny and looking to get laid, she really wasn’t sure why he never had condoms??

As he was pleasuring her, he was taking care of himself with his other hand. He finished pretty quickly, and caught most of it in his hand. But then he just froze there, afraid to touch her for risk of getting her pregnant. “Go wash your hands…” she told him with an impatient laugh. He hurried out to clean himself up and was back quickly to finish the job.

After he got her to where she needed to go, he laid down beside her as she caught her breath. They lay silently for a few moments, and she could hear and feel his breath getting louder, and deeper. He was fucking sleeping!

“Welp!” she said abruptly. “Guess I better be heading out…” He jolted up, “No, no!” he insisted. He apologized for dozing off, and for booty calling her the way he did. At this point she didn’t mind because he had made her finish several times, and she was much more satisfied than she had been with Jason the night before. He asked her to stay for a bit, so they got dressed and moved it back out to the living room… where the porn was still on.

She looked at the tv, then looked back at him. He looked down at her and she bit her lip. So much for getting dressed. He ripped her clothes off her again and pushed her backwards on to the couch. He pleasured her again and again until she couldn’t take it anymore. Geezus. What a fun and unexpected morning!

When it was finally time to go, she got herself ready again and he walked her to the door. As he kissed her goodbye she paused, put her hand on his chest, looked up at him sweetly and said, “Don’t worry, I’m not pregnant”. He rolled his eyes and laughed. “I guess I deserved that one,” he said as she made her way out.

She made it to her bank appointment with plenty of time to spare. As she waited in her car, she saw she had an Instagram notification. It was from Jon. He had seen a workout story she had posted, and had jumped right in to some unprompted dirty talk. Fortunately for him, she had some time to kill before her appointment. Quite an eventful two days for her, geez!

They chatted and flirted for a little while before she had to head in to the bank. He had asked her when she would be coming over again, and she told him that she could probably fit him in that week seeing as her parents were still away, but that they would finalize a plan later on. Jon had to go to work anyways, so she went to her appointment and then headed home.

She and Jon chatted off an on throughout the week, but they weren’t able to mesh their schedules, and had decided to plan for a night later that month when he would have his place to himself. Though she still had some time before her parents came home from their vacation, she was happy to spend the next few days on her own, rather than continuing to see all these guys on a loop. Two guys in two days was plenty.

Continue to Chapter Seventy

Her hookup with Tony was on the Sunday, so early that week she just chilled and enjoyed the peace and quiet of a parent-free house. On the Thursday, however, she had had a girls night planned as one of her besties was in town from out west. She had been looking forward to it for months. It was so nice to see her friend, and to enjoy a fun night with the girls.

Her friend who had hosted the evening lived out in the country, but luckily her visiting friend offered to drive her home. Since she wasn’t DD, she left no wine glass un-drank, and no joint un-smoked. By the time the evening wrapped up and they were headed home, she was feeling all kinds of all right.

She got home around midnight. Drunk, stoned, so obviously horny. She messaged a few of her regular guys, only hearing back from one. -Jason, or Whistler Man (see Chapter 60). Jason was a snowboard instructor out west, but had hurt his back and had moved back home with his parents to await his upcoming surgery.

They had been chatting off and on since his return, but hadn’t met up. He would constantly be commenting on her workout stories on IG, but whenever she asked about hanging out in person he would dodge the question. She knew it had to do with his injury, and she knew he wasn’t as physically able as he had been during their first hook up. But she liked Jason. She would have been fine to even just hang out, but he was making it clearer and clearer that he didn’t want to see her. Only wanted to ogle her from afar, apparently.

That night, with her tipsy thumbs and stoner red eyes, she messaged him saying that she was drunk, and feeling horny and confident. She guaranteed him a good time. To her surprise and delight, he actually jumped at this opportunity and, within minutes, was on her front step.

They rushed upstairs, shut the door, and he grabbed her from her underarms and tossed her on the bed. So far, so. friggin. good! He climbed on top of her and kissed her passionately, but it wasn’t long before he had to lay down. She knelt beside him as he pleasured her with his strong hands, and she attempted to do the same but.. he just couldn’t keep it up.

She realized then that this must be why he didn’t want to meet up with her. Obviously something in his back had affected his nerves, and the poor guy could no longer keep a boner. How sad! He lost both his passions with this injury; snowboarding and sex.

He apologized for not staying at attention, and was gracious enough to help her finish. When she did, his fingers were barely out of her before he said, “well I better go”. She didn’t even have a chance to catch her breath. She scrambled to get her pants back on, while he’s basically down the stairs already. He half hugged her as he rushed out to his car. If he were a cartoon there would have been a Jason shaped hole in her front door, complete with a puff of smoke as he sped away from her. At the time she didn’t care. She knew he was upset, but what could she do to comfort or reassure him if he had already run away from her? “I got mine, so oh well”, she thought to herself, and she went to bed.

The next morning she woke up to a message from Jason. “Hey. Again, I’m sorry about last night. But you and me, can never happen again.”

She re-read the message a few times before simply replying, “all good”. She then unfollowed him. Yes she felt bad for him, but he obviously has a lot of issues if he could be so cold to her after all their chats and intimate conversations over the last several months. He clearly expressed interest in her, and to just end their interactions like that, so abruptly? She knew he had to work his shit out and she was not down to watch him do it. He unfollowed her as well and that was the end of her time with Jason.

Continue to Chapter Sixty Nine

Her encounters with Jack and Yousseff were early in the year. She had decided, as she had many times before, that she would be taking a break from dating. And by dating, she meant hooking up. Several months went by and she hadn’t met up with anyone. She was actually a little bit proud of herself. More surprised, maybe. It just hadn’t been worth it to her anymore. That is until, her parents went away on vacation.

Like a vast majority of people on these dating apps, she lived with her parents. And if she lived with her parents, and all these guys lived with their parents… there’s not a whole lot of places to get frisky. So when her parents went away for ten days in June, she jumped at the chance to fill up her dance card. Her thumbs were a bit rusty, but she began swiping away.

It didn’t take long for her to match with a few guys, one of whom was a tall, broad, dark haired fella with a nice beard. We’ll call him Tony. She had been on a swiping rampage when she swiped right on him, and hadn’t noticed at the time that his profile said ENM (ethically non-monogamous). Normally she wouldn’t have engaged in conversation if she had realized that. Nothing wrong with it, just not for her. She was tired of being a third, or a secret (been there, done that). But in this case, she wasn’t looking to marry this guy, she just wanted a night of fun while her parents were away.

They got to chatting and they hit it off right away. Tony was charming and funny, and like, the nicest guy she had ever chatted with. Not in a push-over way, but just genuinely kind and considerate. She would always apologize when it took her a while to reply as she was used to getting shit on by some guys when she would take too long to respond. This guy flat out said, “we’re all busy, I get it. I’m in to you. I’m not going anywhere”. Swoon, much?!

After a day or two of chatting, Tony added her to Instagram. Almost immediately after accepting his request she got a message from him asking how she knew a mutual friend they had. She explained that it was an old co-worker of hers and that they were still good friends. Then she asked how he knew this person and he replied, “she’s my fiancée’s best friend…”

What the actual fuck!?

Of all the people to match with, of course he knew someone she knew! Again, big city, small town. But really, what are the chances!? Apparently pretty high.

He immediately went in to panic mode expressing how important it was that her old co-worker never find out about this ENM arrangement between him and his fiancée. This person just wouldn’t understand, he said. Not to worry. She was not in the business of ruining people’s relationships. As long as both people consented to being in an open relationship, what business was it of hers to interfere? She assured Tony that she wouldn’t tell her friend, and that even though she still considered this person a good friend, they didn’t speak that much anymore after no longer working together, nor does she read the blog. His secret was safe with her.

They continued chatting. He continued to boost her ego and flatter her relentlessly. She knew she wanted to hook up with him and she was excited to be able to have someone over to her place for once. Unfortunately, that coming weekend, he was busy on the Friday, and she had tentative plans with a friend on the Saturday. Her friend had seemed to be wavering, so she told Tony she would keep him posted. Of course, though, her friend came through so Saturday night was also a no-go.

She suggested he come over on the Sunday afternoon instead. No way was she letting this opportunity pass her by. He agreed and they made a plan to meet at a nearby restaurant first, and to go from there. Friday came and went, but as she was getting ready to go meet her friend on Saturday, she got a message from Tony that started with, “Okay.. real talk…”

He began to explain that he showed his fiancée her picture, and that SHE FRIGGIN RECOGNIZED HER!? How the fu –

Well, it turns out, she had met his fiancée at a party a couple years earlier. Only briefly, but long enough that his fiancée knew who she was… AND knew that she had a blog. So now, Tony’s probably thinking she is some crazy, sex crazed liar who writes about her raunchy sexcapades – which, let’s face it, is not far off – but come on! What a horrible first impression to have of someone!

She explained that she had intended to tell him about the blog the next day when they met, and assured him that she never used real names. This seemed to appease him, and he decided to continue trusting her, and to meet the next day. Why she continued to go along with this encounter, she wasn’t sure. Oh no, yes she was – she was horny AF.

They met at a local pub somewhat in between where they both lived. It was a little awkward at first, but once they got to talking, and to addressing the elephant in the room (this blog), conversation flowed like water. She let him read her favourite chapter (Chapter 49 if you’re interested 😉), and he complimented her on her writing. He also approved of how open she was about her sexual experiences.

They had ordered nachos to share, and as she was about to dig in he said, “wait wait! Gotta show these to the wife” as he snapped a pic to send to his fiancée. You’re on a date with another girl, dude!? Is that not weird for you?? For her??

They ate their meal and continued chatting. When the server came by to ask about another round of beers, she made the executive decision to decline and ask for the bill. She was done stuffing her face and was ready for something else to get stuffed haha (okay yes, that was crude. Sorry. Couldn’t help it lmao)

As they headed out to the parking lot, she suggested she drive them and he leave his car there, and she would drive him back afterwards. She didn’t want his car sitting in her driveway in broad daylight for all the neighbours to see. She lived in a small, close-knit suburban neighbourhood. People talk. Possibly to her parents. No thank you.

As she turned the corner on to her street, she prayed to the Universe that no one would be outside, but it was like 3pm on a sunny Sunday afternoon, the whole damn world was outside! She pulled in to her driveway, and as she got out and came around the car, she saw her neighbour do a double take at this giant man climbing out of her vehicle. Aw fuck! She thought to herself. But oh well, no turning back now!

They went in to the house and she made sure Tony greeted the dog and chilled him out a bit before they went upstairs. They closed the door quickly so the dog couldn’t join them, and then it was sexy time…

Tony pushed her backwards onto her bed and tore her pants off. He climbed on top of her and started kissing her while his hands explored her body. She tried to touch him, but he wanted it to be all about her…

– side note: in her short dating experience, she had rarely been with a guy who was more concerned with his own pleasure than hers. She had been used to having to service her ex first and foremost, before ever getting any herself. All these guys were just a different breed but like, in the best possible way –

The foreplay went on for a while until she was good and warmed up, then they started to have sex. He was definitely a bigger guy. Not fat or anything, but husky. A big, tall, broad, husky guy. Definitely attractive, but being bigger comes with some down falls. One of which, is sweat. As smooth and sexy as this guy was, and regardless of his sexual talents, it’s really hard to keep your head in the game when a stranger is thrusting on top of you, literally sweating globs of salty liquid into your eyes and mouth.

Some might have ended things then and there, but he was such a nice guy! And great at what he did, despite the sweat. She felt bad for him really. He kept apologizing and seemed to be embarrassed. She paused for a moment and grabbed a towel from behind her door. She thought about opening the window, but there was no way she was going to broadcast this tryst to her whole neighbourhood more than she already had. She was definitely not quiet, and her bed was super loud! She was pretty sure all her neighbours had already heard most of it anyways.

Instead of stopping, he suggested they move the fun in to the shower. She had just showered that morning, and immediately thought about how she didn’t want to get her hair wet.. But she also didn’t want to stop, so she bit the bullet and they continued their fun in the shower, where things really got heated.

It was rare for her to experience pleasure while standing up, but Tony knew what he was doing. He also knew how much she loved being choked (likely from reading that blog chapter). So it was just sexual pleasure on a whole other level. Shower sex is actually pretty not bad when you’re with the right person – who knew?

When they finally finished, he waited patiently as she re-blow dried and straightened her hair. He had been sitting on the bed behind her, watching her get ready. As she finished, he put both hands on her hips and pulled her back to sit on his lap, ready to go again. Are you friggin kidding me? I’m not showering again! she thought to herself. They made out a bit, but then headed out again so she could drive him back to his car.

When they got there, she realized she had to buy weed, so he accompanied her in to the pot shop near where he was parked. He helped her pick out her weed, and was super friendly and social with the staff. It really was too bad he was engaged. He definitely seemed like boyfriend material… Hard to get around that sweat issue, though.

They finished buying the weed and she walked him to his car. He hugged her the way only a big, tall, strong guy can, and he kissed her goodbye. Even though she now had this secret between her and her friend, she had really enjoyed herself, and was happy to have seized the opportunity of having an empty house.

Continue to Chapter Sixty Eight

Many months before she had ever matched with Jack (maybe over a year, even), she had matched with another guy on Tinder. We’ll call this guy… Youssef. Youssef was from Jordan but had moved to Canada when he was young. She never got the full story, but his family still lived in Jordan and it was just him living here. He was polite and charming and smooth. He made her feel beautiful. He also had a naughty side and knew how to make her feel sexy and desired. They had chatted for months and months and had never met. First it was lockdown(s), then it was his work and him moving to a new apartment, then the freedumb convoy extended the most recent lockdown and they had just never been able to schedule a date.

Finally, once things had calmed down around town, Youssef asked if she wanted to come over to hang out; “Netflix and chill”, as the kids say. Normally she preferred to meet guys in public, but she and Youssef had been chatting for so long, she already felt comfortable with him, so she accepted his invitation.

She was honestly really looking forward to finally hooking up with him. The tease of their sexy conversations had gone on for far too long, and she was eager to experience some real pleasure, especially after her disappointingly quick encounter with Jack. Yousef sent her his address and she headed over. After she parked and was walking up to his building, she realized that she had been there before in her younger, party girl days. It was an unexpected déja vu to have before going to meet a stranger for a hook up.

She called up to his apartment and he buzzed her in. She barely had a chance to knock on the door before Youssef swung it open and hurried her inside. He was so excited to see her, she could barely get her jacket off quickly enough. Once she did, he threw it on the ground and pulled her in close. “Hi…” he whispered with a smile as she looked up at him from within his tightly wrapped arms. He kissed her and she basically just melted in to a puddle of goo. Butterflies engulfed her entire body and she was instantly ready to climb him like a tree.

He brought her in to the living room where he laid her down on the couch. They started tearing off each other’s clothes, and he climbed on top of her as they made out intensely. His couch was a little bit narrow, though. Kind of a modern design. Not really conducive to an intimate hook up, so she suggested they move it to the bedroom.

They couldn’t keep their hands off each other as they changed locations. She was already down to her underwear, and she could feel him gazing at her basically naked body. Normally she would have felt incredibly insecure. And while, yes, she felt vulnerable, the look in his eyes was one of awe and excitement. She could tell he liked what he saw and she felt powerful and confident and sexy. Not feelings she was used to feeling during a sober hook up.

They laid down beside each other, and while she tried to continue touching him, he stopped her and made it all about her for the moment. He used his big, strong, sexy hands to warm her up and make her feel amazing. It had been quite a while since a guy had been able to get her off. And so many times in a row… She was impressed. She tried to reciprocate but he told her he didn’t want her to. He was getting off by how much he was getting her off. She asked him if he wanted to have sex, but he didn’t have a condom, so she accepted that it would just be him and his hands getting things done. As she finished one final time, he did too. Right on her ribs as he laid beside her.

They both collapsed together in joint pleasure. He wrapped his arms around her and they cuddled together in post coital bliss. After they both caught their breath, he hustled into the bathroom and grabbed a wet cloth to clean her up. Such a gentleman. In her experience of past hook ups, she was expecting to be ushered out shortly after they completed their tryst. But Youssef was sweet and was in no way ready for their afternoon to end. He invited her back out to the living room to watch some Netflix and order some food.

Now that they had addressed the sexual tension that had grown so strongly between them over months and months of texting, they were able to relax and just chat and hang out. They were extremely comfortable with each other, and Youssef was quite open, actually – about his ex-girlfriend, and not being completely over her. He was honest about his downfalls in that relationship, and how he knows, now, what he did wrong. But was also open about some toxic behaviours that his ex demonstrated, which he had let slide in the moment, but saw now how he didn’t deserve to be treated that way.

His breakup was pretty fresh, which she didn’t realize when she had accepted his invite. She also realized why they hadn’t met until that day; he had been going through this breakup when they first connected. She was happy he felt so comfortable talking to her about his feelings, she just hadn’t expected to be imparting her own breakup survival wisdom on this new sexual partner.

Youssef was not what she was expecting, especially in the sense that he was just so open about his feelings, even admitting that he was somewhat in to astrology. Guys are never in to astrology! Most guys would tease her when she brought it up, but Youssef knew his sun, moon and rising signs, as well as his ex’s. He noted some differences between their signs, as well as behaviours he recognized as incompatible.

While she was giving him advice based on her own breakup experience, he noted, “I think it was fate that we met. Even if nothing comes of this, you’re just a really kind, caring, loving person, and I appreciate your thoughts and advice”. She was completely taken aback, but appreciated the appreciation.

She knew that she didn’t want to date Youssef. Just based on their conversation, she recognized that he had a lot of healing to do before he would be fully ready to immerse himself in another relationship. But she agreed with him. She felt like she was meant to meet him and to impart her wisdom. He confided in her that he had a lot of anxiety, but that her point of view on life, dating and breakups had really calmed his soul.

They chatted, and ate pizza, and half watched a stand-up comedy special on Netflix (which now seemed to be her go-to thing on dates?). Once it ended, they both agreed it was a good time to end the evening. He walked her to the door and hugged her tight before she left. Though she knew that would likely be the only time they’d hook up, she left feeling relaxed from fooling around, but content in her heart after making a new friend.

She went home and enjoyed the rest of her night. She went to sleep at a reasonable hour, but was tossing and turning around midnight. It was then that she happened to glance over at her phone, and saw it light up. She picked it up and saw message after message coming in from Youssef.

“I’m sorry to bother you!” “I know it’s late” “But is there any chance you could be pregnant after today?” “I know we didn’t have sex but like, when was the date of your last period?” “Do you think some pre-cum could have gotten inside?” “Please. I’m having a panic attack. My family is so religious. They would disown me if I got someone pregnant…”

She hadn’t intended on replying at first, but it was obvious he was having a friggin mental breakdown. She was extremely confused though because, this was a 31-year-old man who was not a virgin. Had been in a sexual relationship for 5 years with his ex. The basics of sex should have been pretty clear to him, no? How on earth could he think she could be pregnant when he finished on her ribs?? On her RIBS! No where near the danger zone.

She sat up and texted him, reassuring him that there was absolutely no way she could be pregnant. Not only did they not have sex, but even if they had, she has PCOS and doesn’t ovulate. So even if they HAD had sex without a condom, on the perfect day of the month, the day that she would ever be closest to ever being able to get pregnant, even then, she still likely wouldn’t be. And again, she reminded him, HE CAME ON HER RIBS!

Youssef seemed to calm down, and repeatedly apologized for bothering her so late. He thanked her profusely for her kindness and patience at 12:30am on Sunday night. She wouldn’t have been able to sleep had she ignored him, so she told him it was fine and that they could chat again another time.

The next day on her lunch break at work, she messaged Youssef to see if he was okay. He apologized again for freaking out like that. He knew that logically, there would be no way that she could have been pregnant. Anxiety is real bitch, though. She understood. And she was glad he seemed to be doing better. Still, though, that just confirmed that there was absolutely no way anything else could ever happen with this guy.

She had worked hard on her own healing and knew that she couldn’t have done it if she had gotten mixed up with someone else during that time. It was better for him to be alone and to work on himself. She stopped texting him, and he eventually stopped texting her. She knew that if either of them ever did message the other again, neither would ghost the other. But it was just better that they end things there. Meeting Youssef made her even feel even more grateful for how far she’d come in her own journey. She remembered all those feelings that Youssef was demonstrating, and she was proud of herself for having come out of it the way she had.

Continue to Chapter Sixty Seven

After her disappointing second “date” with Jon, and ol’ Needle Dick having unfollowed her on Instagram, she felt completely uninterested in dating whatsoever.

It was now January 2022. Another lockdown. Another month of work, then home, and back again. What would have been the point in dating? She had turned off all her notifications from all her dating apps, but sometimes would find herself going a little stir crazy, so every now and then, she’d check in on the sad selection of guys her apps had at the ready.

She opened Hinge, and found a guy named Jack had sent her a “rose”. She checked out his profile and, according to his answers to the prompts he chose, he really did seem like an interesting fella. He came off as charming and confident and funny and sweet. However, he looked like the Canadian version of Pauly D (Jersey Shore). Hair not quite so hard and helmet like, and skin much less orange, but that same greased up sleaze ball look. The gold chain was the cherry on top. She really debated whether or not to match with him. Physically, he didn’t seem like her type, but his answers were great and she knew that her “type” never ended up being good for her. So she took a chance and matched with Jack.

It was a day or two before he sent her a message. Again, he was charismatic and funny and charming. Turns out, he lived somewhat on the outskirts of the downtown core, but was house/dog sitting for his friend who lived close to where she worked in the west end of town. He asked if she wanted to come by one night. She appreciated the interest he had in her, but didn’t feel comfortable meeting for the first time at a strangers’ friend’s house. Instead, she suggested they meet for coffee at the Starbucks near her work. If they hit it off, they could see where things went from there. He agreed, and they made plans for that coming Friday.

She arrived at the Starbucks before he did, but knew that the big, black pick-up truck that pulled in a few spots down from her, had to be him. He got out of his vehicle and started walking towards the building. He met her gaze as she spotted him walking, and she got out of her car to greet him. He wanted to go in for a hug but she goofily dodged it in to an elbow tap. Even though she had hooked up with several guys throughout the pandemic, she still tried to be cautious upon first interactions. They went and ordered their coffees, and he gallantly offered to pay. That might not seem like a big deal, but she really never did expect her dates to pay, and Starbucks is expensive! So it was a pleasant and welcome gesture on his part.

She wasn’t sure what the plan would be from there. Because of lockdown, they couldn’t sit and chat inside, but it was January so it was still cold AF outside. A stroll around the block was also out of the question. He suggested that they keep warm in his truck. On one hand she thought, “What if he drives away and kidnaps me?!”, on the other, more logical, hand, she knew the odds of that actually happening for real, were pretty low. She agreed and climbed in to his truck to drink their coffees and chat.

She noticed right away that he was nervous. He wouldn’t shut up. Even when he’d ask her questions, she’d start answering and then he’d interrupt with his own anecdote. Yes, that was frustrating and very mansplain-y of him, but she could tell it wasn’t coming from a rude place. He seemed genuinely interested in her. And still, she couldn’t decide if she was in to him or not.

As a friend, she knew he’d be great. But as anything more, she was still on the fence. That alone should have been her red flag that no, she wasn’t in to him. But again, every guy she *was* in to, turned out to be a total D-bag. It was the fact that she wasn’t super in to him that made her want to try harder to find something romantically interesting about him.

They chatted for a while about this, that and the other thing. Obviously they touched on sex. Jack boasted politely about his sexual prowess. He told her that of the few girls he had been with, they had all told him that he was incredible in bed. She knew that for him to say that meant that he likely wasn’t the sex king he claimed to be, but she let him continue with his narrative. It was then that he mentioned that he hadn’t lost his virginity until he was 35 years old. THIRTY FIVE! (She thought her losing it at 22 was late) If she wasn’t sure before, she definitely was now, that he most certainly was not the sex god he said he was.

They talked until it got dark. Despite his lack of experience in the bedroom, he remained a fairly interesting conversationalist. Still, if he had invited her back to his friend’s place, she probably wouldn’t have accepted. Thankfully, she didn’t have to make up any excuse because, and these were his exact words, “I’d love to have you over, but truthfully, I bailed in the shower earlier and I tweaked my neck. It hurts to just turn and look at you, so I really should go home and take care of this…”

She tried so hard not to laugh. Not that she found his pain funny, but that is just such a believable excuse. Definitely something she would do and could relate to. He got out of the truck and she allowed him a quick little goodbye hug. He was tall and brood, so for the split second that he had her in his embrace, she thought, “hmm.. maybe there could be something here?”

They said their goodbyes and she then broke every speed law imaginable trying to get home before she peed her pants. He had ordered her a Venti and she drank the entire thing, but couldn’t pee at Starbucks because of lockdown. She had never rushed home from a date faster than she did that night. (Don’t worry, people. She made it in time 😉)

During their truck chat, he had asked about getting together again sometime. She suggested the next day seeing as it was lockdown and she consistently had zero plans, and even though it likely wouldn’t be the sexcapade of her dreams, she seemed to be enjoying his company. He, however, did have plans, so they just left it open ended.

Saturday, early afternoon, he sent her a message and they got to chatting again. He had said that his plans got canceled and asked if she still wanted to get together. It had been a very lazy Saturday so she was still in her PJ’s, but it was only like 5pm. She had plenty of time to shower and get ready, so she decided to take him up on his invite. She told her parents she was off to see a friend, punched the address into Google Maps, and headed on her way.

When she arrived at Jack’s friend’s place, her jaw dropped. It was a literal mansion. Like, 10 car driveway, double front doors, grand entrance, spiral staircase, 10 bedrooms, 7 bathrooms… truly, a fucking palace. He gave her a tour of the main floor, and as they strolled in to the living room, she saw a beautiful, old, grey Pitbull curled up on the couch, wearing a cone of shame.

The dog had just had emergency surgery before his friend had to go away on business and needed extra care while he was away, so Jack was there taking care of her. Okay, major hot points right there. They sat on the couch and put on some random stand-up comedy special on Netflix while they got to talking. The dog took to her immediately and crawled right over to her, positioning herself between her and Jack. She was kind of relieved by to be honest, because then Jack couldn’t put any lame moves on her.

Eventually, Jack suggested he give her a tour of the rest of the house. She accepted, knowing full well they would end up in the bedroom. She knew that if she had said no to having sex that Jack would have respected that. She could just tell he was a genuinely nice guy, which is probably why she wasn’t super in to him. That, and the fact that she couldn’t get his lack of sexual experience out of her mind.

When they got to the bedroom, he inevitably tried to kiss her and get things going. She decided to just go with it. Who knew? Maybe he had learned something from the few girls he’d hooked up with? Maybe he would blow her away with his “incredible” bedroom skills (his word, not hers) and then finally she could prove to herself that she was capable of finding a genuinely good guy to be with.

The kissing was decent. Which then led to foreplay, which was not so decent. Very rushed. Not nearly enough time was spent getting her warmed up. Then, before she knew it, condom was on and they were having sex. Missionary style seemed to be his preference. And while that’s all well and good, having this strangers’ face right up against hers while he panted and grunted and thrusted away, just really wasn’t doing it for her.

She suggested they switch things up and start with some doggy style. At least that way he wouldn’t be all up in her face. Unfortunately for Jack, “Little Jack”, had quite the significant curve in it. Like, it literally looked like a small banana the way it curved up so much. “Maybe that’s why he was a virgin for so long?” she thought. “Maybe he had crippling insecurity over his banana dick?” (Get your head back in the game!)

Jack had been able to maintain a good rhythm while doing it missionary. However, after switching positions, Jack didn’t stand a chance. He finished in record time, and she realized then why he preferred missionary; his curved weiner was just way too sensitive any other way. He hurried off in to the ensuite bathroom to clean himself up, while she got herself dressed.

They went back downstairs to the poor little Pitty who was so sad to have been left alone. Good thing they weren’t gone for very long. She cuddled up to the dog again and they resumed their comedy special. It was about 10pm when it finished, and she took that as a good opportunity to bring their evening to a close. Jack saw her to the door and kissed her on the cheek as she left. It was a pleasant enough encounter. However, despite her best efforts, she knew she couldn’t force feelings that just weren’t there. She needed a guy who would challenge her, but who would also be sweet and kind – a bad boy with a heart of gold, to be so cliché.

Jack messaged her a couple times over the next week or so. She always responded, she definitely didn’t ghost him – but he eventually got the hint that she wasn’t interested in another date. He was a nice enough guy, but hooking up with him was the last straw for her.

She was sick of disappointing sex. She was sick of re-telling the same spiel to guy after guy, knowing full well they didn’t really care, just like she didn’t care about their stupid lives either. She was ambivalent towards dating now. She had said it over and over throughout the pandemic, but this time, she had really had it with online dating… (yeah, right…)

Continue to Chapter Sixty Six

She was happy to have heard from Jon again, and that her little injury didn’t deter him or turn him off. She was looking forward to seeing him, this time for a real date. They agreed to meet up that coming Friday at a nearby restaurant. She loved that he lived so close and that she didn’t have to go downtown to see him.

She arrived shortly after him, and found him seated at a booth on the bar side of the restaurant. Jon got up and hugged her hello, and they eased in to some comfortable conversation. This was the first time they’d hung out, both completely sober. The first time they’d met, he was drunk. The second time they’d met, they were both drunk. So this time was really the make-it-or-break-it date.

After the initial pleasantries, he let out a big sigh and began venting about his family situation. Jon was one of 4 siblings. He and his brother shared the same dad, but his mom had had his younger siblings with another man – his dad’s brother, to be specific. His younger siblings were also his cousins! She was hooked. She could have listened to that family drama all night! But then he got in to the fact that one of his sisters isn’t vaxxed, so they can’t go see this family member or that family member because of it. There’s now a big rift in the family, bla bla bla.

She was empathetic and supportive, at first. But he just kept rambling on about it. Whenever the Covid conversation seemed to be coming to a natural end, like she’d be able to change subject, he’d just start repeating himself again. Obviously it was weighing on him and she felt bad for him, but if she wanted to discuss Covid and the pandemic, she could have just stayed home and turned on the news.

Eventually, she was able to guide the conversation to a more light hearted subject, but she found that no matter what she said, Jon constantly interrupted her with whatever relatable story he had, never letting her finish her own. V annoying.

Soon, the food arrived. She had ordered a spicy chicken appetizer, he ordered a personal pizza. As she began to cut a piece of chicken, Jon just started shoveling his pizza in like he had just gotten out of prison and hadn’t eaten a real meal in years. Not only that, he continued to talk as he ate. Continuing to interrupt her as he mowed down on big wads of sauced up dough. Not sexy.

They finished their meals and drank up the rest of their drinks after agreeing that they’d continue their evening back at his place. She may have been turned off by his table etiquette, but she was still down to fool around after having had such a good time before. He had walked over to the restaurant because he lived so close, so he hopped in her car and she drove them back to his parents place. They were out again, and she thought about how she wished her own parents could have as busy a social life as Jon’s parents seemed to.

They went downstairs and settled in to his bed together. He put on some random show on Netflix, and the make out sesh began. His kissing was a lot sloppier than she had remembered. Also, was he this friggin skinny the last time they hooked up? She could feel his bony shoulder blades protruding from his back as she wrapped her arms around him. She was definitely not as in to it this time as she had been the time before, but “maybe he was just a slow starter?” she thought. He moved his way down to start warming her up, but again, just not the same as last time.

Soon, they switched positions and he was laying on his back. She started giving him a BJ, and within a few short minutes, he was pushing her off of him so he could finish. Her intent was not to get it to that point, she was just trying to get him to stay up. Turns out, he had had like 3 beers before meeting her at the restaurant. Including the 2 beers he had when they were out, apparently he was pretty drunk and she never even realized it! He held his composure pretty well, but so much for them both being sober! (🙄)

He grabbed a nearby towel and did his thing. “Awesome“, she thought. “Now what?” He was still willing and eager to help her finish, but the mood had pretty much passed. She really had tried to give him the benefit of the doubt, but she realized she should have trusted her gut at the restaurant when she was initially turned off.

After Jon cleaned himself up, he offered to go grab them some water. She got dressed and checked her phone as he left the room. To her surprise and delight, there was a message from Brady. She hadn’t spoken to him in a little while, but after that disappointing hook up, she was genuinely happy to hear from him.

The text was from an hour or so prior, asking what she was up to that night. She thought about lying and saying she was just with a friend, but their “relationship” (if you could even call it that) had developed in such a way that not only could she tell him she was on a date, she could tell him she had just had a lame hook up and she knew he’d be interested. She quickly replied as Jon came back with two glasses of water. He handed her hers, and asked if she wanted to go check out his “man cave”.

Jon showed her out to the backyard. There was a large structure in the back corner. Not exactly a guest house, but definitely bigger than a shed. It was weird, but also kind of cool. They walked in and it was literally just a stoner shack. That’s where he and his brother kept all their weed and paraphernalia, complete with a ratty old futon, an old, torn up La-Z-Boy, a big screen and a mini-fridge.

She sat down on the edge of the recliner as Jon attempted to get the TV to work. Then he sat down and began to roll them a joint. As he was rolling, she read Brady’s reply. He asked her to come over, but she replied to him that she couldn’t because she was still with Jon. He teased and asked her to send him a pic, so she candidly took a pic of Jon’s foot and the TV on the wall behind him. Brady told her to come over when she was done, and she agreed to text him when she left.

Jon took a hit of the joint and passed it to her, which she accepted, knowing she’d then have to stay a little while longer. It was good weed, but as she sat there getting stoned with him, she realized there were now truly zero sexy vibes between her and Jon, at least on her end.

Looking at him now, he looked like just some punk kid. He was skinny and gangly and not as funny as he thought he was and just.. ugh. She had learned that being the “older woman” could be fun, but in that moment it just felt pathetic. She wanted to leave but had just taken that hit from the joint so she had to wait it out a little while longer. Jon, on the other hand, smoked the whole thing and was now glassy eyed and goofy. She knew he had no idea that she was regretting this little tryst.

About half an hour later, she felt comfortable enough to drive. Jon walked her back to the main house so she could grab her things, and he kissed her goodbye at the door as she left. As she shut the car door, she texted Brady letting him know she was leaving. She had been so disappointed by this date, the thought of a make-up hook up seemed too enticing to pass up. After texting Brady, she thought to herself that if he replied right away, she’d go see him, but if he hadn’t replied by the time she drove passed his house (or like, the street that would take her to his house), then she would just go home. Not surprisingly, she ended up just going home.

The next day, she had some errands to run so she was up early. She checked her phone when she woke up and saw a message from Brady from like 2:30am. She replied to him that she hoped he had a fun night, to which he surprisingly replied quickly. He said that he did have fun, and asked if she had fun hooking up with that guy. She told him that it was a less than satisfactory encounter, and he suggested that she come by that day so he could make it up to her.

Now, the first time she and Brady had hooked up, similar to her first time meeting Jon, he was drunk and she was not. It was not great, and she reminded herself of Brady’s skinny little wiener. However! This time he would be sober and would likely be better adept at meeting her needs. She told him that she was down to come over, but that she had some errands to run first. She said she would only need like an hour, and then she’d stop by. He agreed and told her to text him when she was done.

This was mid-December, so her errands included fighting crowds at the mall and sitting in traffic. It took her about 2 hours to get everything done, but when she got back in to her car in the mall parking lot, she texted Brady that she was ready to come over. She sat there, waiting for him to reply. Waiting. And waiting. And waiting. She waited a good like, 12 minutes before texting him again. He replied quickly to her second text, but completely side stepped her question about her coming over. So she asked again, and then again no reply.

She sat there in her car, now completely enraged. Was she the one to start texting him again? No. Was she the one who asked to go over that day? No. Why text her at all if he didn’t want her to come over? Why even suggest or hint at it? AND, say he had initially been down but then got caught up in something, why not just tell her?? Why ignore her?? Why was he fucking with her?? Uuuggghhhh!!

She wrote some version of those thoughts and sent him another message. He replied, “Oh stop, you’re fine” which made her want to smash her phone in to a million pieces. Instead, she sent him an eye roll and middle finger emoji and shoved her phone back in her purse. Then she drove home. Fuck that guy, and his skinny, useless wiener.

Two shitty experiences with two separate guys in less than 24 hours was enough to turn her off of dating for that moment. It was just before Christmas, she knew it would be a lot of family time coming up, so she decided to just let it all go and focus on the good. Christmas came, she had a wonderful day with her family, and even though she didn’t really get any holidays that year, she enjoyed her time off as best she could.

She had to work throughout the week between Christmas and New Years. For months prior she had been over the moon excited about her New Years Eve plans to go to Montreal with her friend and her husband (Not a third wheel, a Throuple. There’s a difference 😉). However, like literally everyone else, her NYE plans got canceled when the Covid protocols changed.

Not only was she disappointed at not being able to go away for the weekend, she had also arranged to meet up with a guy she had met on Tinder months earlier. He lived in Montreal so they had yet to meet, but they’d stayed in touch since they first matched, and she was so looking forward to a fun night with him. Instead, her New Years plans now consisted of dinner and a movie at home with her parents. Could have been worse, of course. But still, it was not what she had hoped for.

While she and her parents were watching the movie, she saw her phone light up. It was a text from Brady. She rolled her eyes when she saw his name, but then also immediately opened it. “New years plans?”, was all it said. She waited a good 10 minutes before replying, and when she did she told him that she had hoped to be hooking up with a hot guy from Montreal, but that her plans got canceled.

“Wanna come over? I could try to find another girl to come by, too…” Brady replied. She was taken aback by the random inclusion of another woman, and wondered why he would think she’d just all of a sudden be down for a threesome. She replied “No thanks,” to the ménage a trois, but said maybe she’d be down to hang out just the two of them. He hmm’d and haah’d and tried to lessen the blow to the fact that he already had a girl coming over.

“So… I’m the other girl then?” she asked incredulously. “Why didn’t you just say that? ‘I’m having a girl over tonight, wanna join?’ Why pretend I was your first choice?” He didn’t really have an answer, he just laughed and brushed over it. “Well, no thanks, I’m good. Have fun…” she texted. “You have fun too,” he replied. She was still surprised at the random question, but was also super annoyed. Not only with Brady, but with herself for letting him get under her skin like that. Why were gingers always such ass holes, and yet were always able to maintain such a hypnotic hold over her?

New Years came and went, and she was back to work the following Tuesday. As she was scrolling through Instagram on her lunch, she saw a new post from Brady. She clicked on it, and for some reason, something inside of her just told her that she needed to check if he was still following her. Sure enough, the fucker had unfollowed her because she turned him down on NYE.

Fuck you, Needle Dick!! She unfollowed him immediately.

She was so mad. She was also mad because she hated how mad she was. She was mad because, yet again, she had become hooked on a guy with zero potential for anything (not even a good hook up!) and yet she still yearned for some kind of acceptance from him. Well! Not today, Satan. Not today.

That was is it. That was the moment she realized that she was wasting her time and her potential on guys who weren’t even worth a second look, let alone worth agonizing over. It was this revelation that led her to the epiphany that she needed to get back to focusing on herself, rather than the validation she felt from male attention. (Click here to elaborate).

In 2022, she vowed to make herself and her own happiness Priority Number One. Dating would be shifted to the back burner and, unless someone amazing came along, that is where it would stay until she was able to get the rest of her life in order.

Continue to Chapter Sixty Five.

She saw Jon waiting for her on the front lawn of his parents house as she got out of the cab. She hurried towards him and he ushered her inside. His parents were away, so he had also been hanging out with friends earlier, and was just as drunk as she was. The perfect recipe for a messy night of fun.

He escorted her to the basement which was pretty decked out, actually. It had a finished, full bathroom, a nice little living room set up, and Jon’s bedroom was at the end of the hall. His bedroom was just as nice. Big enough for his own little living room area, with his bed up against the wall underneath a fairly large window for a basement.

As soon as he shut the door, they just went at it. He tore her coat off her and threw off her shirt, barely giving her a chance to undress him as he ripped his own shirt off and pushed her onto the bed. They made out intensely as their hands wandered ferociously all over each other’s bodies. She unzipped his pants and gave him a quick handy-j, but he was more interested in pleasing her.

He pulled her bottoms off and got her good and warmed up, to put it delicately. It felt amazing and she was loving every second of it. The foreplay went on for a while before he grabbed a condom and they started to have sex. Unsurprisingly, he couldn’t really get it up. Well, he could get it up, he couldn’t keep it up. Beer will do that. So, instead of letting that ruin the night, he just continued with the foreplay. Just on and on. Rough, messy, drunken, euphoric orgasms over and over again.

Eventually, when she couldn’t take it anymore, she begged him to stop. He collapsed beside her and they both settled to catch their breaths. She glanced over at the clock on the wall, 4:15am. Shit. She definitely had to get going. They cuddled for a little while until they had both fully come down from the high that amazing sex will give you (or amazing foreplay, same diff). She called a cab, which said would it would be at least 20 minutes, and got herself dressed.

As she stood there in her leggings and bra, looking for her shirt, Jon looked up at her from the edge of the bed and said, “you’re so fucking gorgeous!” He lunged towards her, wrapping his arms tightly around her waist, pulling her back on top of him as he lay back on the bed. They shared a passionate kiss but she had to stop it for fear of getting too worked up and missing her cab. She finished getting dressed and they went out to the living room area to watch for her ride out yet another large basement window. The cab was taking forever, and it was then that she started to feel dizzy. She was definitely still drunk, and was dreading the hangover she could feel looming over her.

They got to talking as they waited, discovering things about each other that people typically discuss before having sex. She never was one to follow the norm. As they waited and waited, Jon began getting worked up again. All of a sudden he sprung himself off his side of the couch, pushed her back into a more reclined position, shoved her coat up and lowered her pants just enough that he could go down on her again, fingering her as rough as he had when they were really in to it earlier. His mouth felt good, but she was definitely not warmed up enough for him to be ramming his fingers all up in there. As she was about to tell him to stop anyways, she saw the headlights from her cab shine through the window. She pushed him off as she jumped to her feet and fixed herself up. Both of them laughing at how they ended up.

He walked her out to the cab and kissed her goodbye. They both agreed that they’d be seeing each other again. She loved the fact that he lived so close to her. In no time, she was home, in bed, ready to sleep away the next day.

She slept all day Sunday, and went to work still hungover on Monday morning. As she lounged about in her bed on the Sunday, she had felt some mild discomfort in her downstairs area, but assumed it was just her body recuperating after her fun night with Jon. The Monday morning when she got up for work, it hurt a little bit when she peed. Again, though, she just thought it was the normal aftermath from Saturday. When she arrived at work, however, and had to sit in an office chair for 8hours, she became increasingly more uncomfortable.

She went to the bathroom with her cell phone, locked the door, and gave herself a wee li’l looksy. She couldn’t see anything, really, but she noticed she was a bit red and swollen. Again, she just thought it was normal after all the rough, orgasmic foreplay Jon had performed on her. She washed her hands and went back to her desk, assuming she’d feel better soon.

By the Tuesday, she had gone from mild discomfort, to full blown pain. She couldn’t pee without the sensation of hot, burning, fire, so she had to spread herself open and push out hard so her pee came out quickly and didn’t risk actually touching her. She couldn’t sit at her desk all day unless she adjusted her legs beneath her in just the right fashion. Then, of course, her legs fell asleep and she would have to suffer through the painful re-adjustments.

She was starting to spiral. Was this an STD? Did she have a UTI? Had he fingered her so hard and deep that he tore her cervix up or something? What the hell was going on down there that hurt so fucking much??

Whenever anything happens to her during a drunken stupor, she immediately feels a wave of guilt and shame. This is exactly what happened to her when she realized the pain she was feeling was more serious than originally thought. She told herself she was disgusting. That she was a dirty slut who had brought this on herself. Of course this happened to her. Nothing good ever comes from her getting drunk. She fell deeper and deeper into her shame, and didn’t tell anyone for fear of being looked down upon for yet another bad choice she had made.

Fortunately, when she wasn’t sitting or peeing, she felt nothing. This was a great relief because it allowed her to continue working out to get out her stress and frustrations. On the Wednesday night, as she was finishing her workout, she got a message from Jon asking how she’d been. She still hadn’t told anyone about this, so when he asked, she thought, what better person to confide this to?

She told him all about it and he was extremely apologetic. They concluded that it must have happened as they were waiting for her cab and he had tried to finger her again without really warming her up. She felt better now that she wasn’t in this situation alone, and Jon really was great about not making her feel dirty or gross. When the pain still hadn’t subsided by the Thursday morning, she placed a teary-eyed phone call to her doctor.

Her doctor had been seeing her since she was very young. Dr. Laura, we’ll call her. Not only had Dr. Laura known her for most of her life, she also treated her entire family. The thought of having to explain this to Dr. Laura made her want to crawl in to a hole and die. She knew she had no other choice, though.

The receptionist answered, and she couldn’t help but sob as she explained her situation. The receptionist, bless her heart, realized how urgent this was and scheduled her in for an emergency appointment that evening with the on call doctor. YES! She wouldn’t have to see Dr. Laura!

She raced over to her doctor’s office right after work. She was shown to an examination room almost immediately. Then, of course, it was like half an hour waiting in there for the on call doctor. When the doctor finally did come in, she was surprised at how young she was. Not only that, the on call doctor was waaayyy too peppy for her present state of mind. She cringed at the thought of having to show this lady her broken vagina, but really, what choice did she have?

The on call doctor had her lay back on the examination table, putting the soles of her feet together and opening her knees wide. With a light on her head and gloves on her hands, the on call doctor got all up in her business trying to see where the pain was coming from. A-ha! There it was! A small cut on her inner labia. Nothing a little vaseline to moisten the area couldn’t fix!

As soon as the on call doctor gave her the good news, she immediately broke down in like, hysterical tears. The wave of relief that had come over her was all consuming. She thanked the doctor and apologized for the awkward appointment, to which the doctor laughed and replied, “Next time, maybe try some lube?” She was mortified to think that this doctor thought she didn’t know the basics of sex, but she let it go and got herself dressed.

She went home and packed herself a little tupperware of vaseline so she could bring it to work to reapply as necessary. She also lathered herself in it that night. In a few days, she was back to normal. Pain free and ready to pee!

At that point, she had finally confided in one of he friends about this whole situation, and how shitty she felt about herself. Her friend was so supportive and made her realize that it wasn’t as bad as she was making it out to be. Shit happens, she didn’t need to keep punishing herself for it. She had gone and gotten it taken care of, and now she could move on.

She told herself she wasn’t going to let herself get in to another mess like that again (how many times had she said that in her life? 🙄) , so when she heard from Jon later that weekend, asking how she was feeling and if she’d be up to seeing him again, she agreed, but insisted they go on a real date. If she were to hook up with him again, she wanted to be sure she’d remember it and that she’d be fully aware of her actions. He agreed, and they set the date for the following Friday…

Continue to Chapter Sixty Four